DE68928516D1 - Process for the preparation of optically active glycidate esters - Google Patents

Process for the preparation of optically active glycidate esters

Info

Publication number
DE68928516D1
DE68928516D1 DE68928516T DE68928516T DE68928516D1 DE 68928516 D1 DE68928516 D1 DE 68928516D1 DE 68928516 T DE68928516 T DE 68928516T DE 68928516 T DE68928516 T DE 68928516T DE 68928516 D1 DE68928516 D1 DE 68928516D1
Authority
DE
Germany
Prior art keywords
ester
product
methoxyphenyl
disclosed
production
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
DE68928516T
Other languages
German (de)
Inventor
David R Dodds
Jorge L Lopez
Charles M Zepp
Steven Brandt
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sunovion Pharmaceuticals Inc
Original Assignee
Sepracor Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from US07/309,769 external-priority patent/US5274300A/en
Application filed by Sepracor Inc filed Critical Sepracor Inc
Application granted granted Critical
Publication of DE68928516D1 publication Critical patent/DE68928516D1/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/48—Compounds containing oxirane rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D281/00—Heterocyclic compounds containing rings of more than six members having one nitrogen atom and one sulfur atom as the only ring hetero atoms
    • C07D281/02—Seven-membered rings
    • C07D281/04—Seven-membered rings having the hetero atoms in positions 1 and 4
    • C07D281/08—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
    • C07D281/10—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
    • C12P17/02—Oxygen as only ring hetero atoms
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P41/00—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture
    • C12P41/003—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by ester formation, lactone formation or the inverse reactions
    • C12P41/005—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by ester formation, lactone formation or the inverse reactions by esterification of carboxylic acid groups in the enantiomers or the inverse reaction

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Wood Science & Technology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Zoology (AREA)
  • Health & Medical Sciences (AREA)
  • General Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Biotechnology (AREA)
  • Biochemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Microbiology (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Analytical Chemistry (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

This invention relates to a method for the production of (2R,3S)-3-(4-methoxyphenyl)glycidic acids and esters thereof, which are synthetic intermediate for the production of the calcium antagonist diltiazem. The method involves the stereoselective enzymatic ester hydrolysis of racemic trans-3-(4-methoxyphenyl)glycidic acid ester to yield the resolved (2R,3S) compound as the ester. Membrane reactor methods and apparatus for the conduct of this enzymatic resolution process are also disclosed herein, as is the use of bisulfite anion in the aqueous reaction phase as a means of minimizing the inhibitory effect of an aldehyde reaction by-product on the reaction's progress. The benefits of selected solvent systems from which may be obtained highly resolved ester product are also disclosed. These enriched organic solutions may be used in subsequent transformations. Alternatively, optically pure product may be obtained directly therefrom. <IMAGE>
DE68928516T 1988-10-26 1989-10-26 Process for the preparation of optically active glycidate esters Expired - Lifetime DE68928516D1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US26517188A 1988-10-26 1988-10-26
US07/309,769 US5274300A (en) 1988-10-26 1989-02-10 Enzymatic hydrolysis of glycidate esters in the presence of bisulfite anion
US07/335,636 US6521445B1 (en) 1988-10-26 1989-04-10 Process for preparing optically active glycidate esters

Publications (1)

Publication Number Publication Date
DE68928516D1 true DE68928516D1 (en) 1998-02-05

Family

ID=27401773

Family Applications (2)

Application Number Title Priority Date Filing Date
DE68928516T Expired - Lifetime DE68928516D1 (en) 1988-10-26 1989-10-26 Process for the preparation of optically active glycidate esters
DE68923883T Expired - Lifetime DE68923883T2 (en) 1988-10-26 1989-10-26 METHOD FOR PRODUCING OPTICALLY ACTIVE GLYCIDATE ESTER.

Family Applications After (1)

Application Number Title Priority Date Filing Date
DE68923883T Expired - Lifetime DE68923883T2 (en) 1988-10-26 1989-10-26 METHOD FOR PRODUCING OPTICALLY ACTIVE GLYCIDATE ESTER.

Country Status (9)

Country Link
US (1) US6521445B1 (en)
EP (2) EP0440723B1 (en)
JP (1) JP2693248B2 (en)
AT (2) ATE126541T1 (en)
AU (1) AU4497289A (en)
CA (1) CA2001515C (en)
DE (2) DE68928516D1 (en)
IL (1) IL92122A (en)
WO (1) WO1990004643A1 (en)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL8801311A (en) * 1988-05-20 1989-12-18 Stamicarbon PHENYL GLYCIDATE STEREOISOMERS, CONTAINING PRODUCTS THEREOF WITH 2-NITROTHIOPHENOL AND THE PREPARATION OF DILTIAZEM.
JP2687789B2 (en) * 1991-08-13 1997-12-08 田辺製薬株式会社 Process for producing optically active 3-phenylglycidate compounds
FI93833C (en) * 1992-05-14 1995-06-12 Orion Yhtymae Oy Process for the preparation of propionic acid derivatives
US5273895A (en) * 1992-10-26 1993-12-28 Sepracor, Inc. Enantioselective production of chiral carboxylic acids
NL9202208A (en) * 1992-12-18 1994-07-18 Dsm Nv Method for the enzymatic preparation of optically active glycidic acid esters.
EP0710725A1 (en) * 1994-11-01 1996-05-08 Takeda Chemical Industries, Ltd. Production of optically active compounds
TW438787B (en) 1997-02-27 2001-06-07 Tanabe Seiyaku Co Process for preparing optically active trans-3-substituted glycidic acid ester
US6461858B1 (en) 1998-01-26 2002-10-08 Pharm-Eco Laboratories, Inc. Enzyme activated supports for enantiomeric separations
WO2014030106A2 (en) * 2012-08-18 2014-02-27 Unimark Remedies Ltd. Process for preparation of optically active (2r,3s)-3-(4- methoxyphenyl)glycidic acid methyl ester and cis lactam and uses thereof

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3635795A (en) * 1968-12-27 1972-01-18 Merck & Co Inc Enzymatic resolution of racemic (cis-1,2-epoxypropyl) phosphonic acid compounds
US4585768A (en) * 1984-04-10 1986-04-29 Tanabe Seiyaku Co., Ltd. 1,5-benzothiazepine derivatives and processes for preparing the same
US4732853A (en) * 1984-11-21 1988-03-22 President And Fellows Of Harvard College Method of making chiral epoxy alcohols
IT1189069B (en) * 1986-03-14 1988-01-28 Donegani Guido Ist BIOTECHNOLOGICAL PREPARATION PROCESS FOR L (-) - CARNITINE CHLORIDE
DE3785132T2 (en) * 1986-04-16 1993-10-21 Sumitomo Chemical Co PRODUCTION OF OPTICALLY ACTIVE CYCLOPROPANIC CARBONIC ACIDS.
JPS6315398A (en) * 1986-07-07 1988-01-22 株式会社東芝 Terminal for monitoring state
US4800162A (en) * 1987-04-01 1989-01-24 Sepracor, Inc. Method for resolution of steroisomers in multiphase and extractive membrane reactors
JP2627627B2 (en) * 1987-11-09 1997-07-09 昭和飛行機工業株式会社 Refrigerated container
NL8801311A (en) * 1988-05-20 1989-12-18 Stamicarbon PHENYL GLYCIDATE STEREOISOMERS, CONTAINING PRODUCTS THEREOF WITH 2-NITROTHIOPHENOL AND THE PREPARATION OF DILTIAZEM.
FI95931C (en) * 1988-09-02 1996-04-10 Tanabe Seiyaku Co Process for the preparation of the lower alkyl ester of (2R, 3S) -3- (4-methoxyphenyl) glycidic acid
JPH0678A (en) * 1992-06-22 1994-01-11 Fujiwara Techno Art:Kk Humidification of solid culture apparatus with air-conditioner

Also Published As

Publication number Publication date
CA2001515C (en) 2005-05-10
CA2001515A1 (en) 1990-04-26
AU4497289A (en) 1990-05-14
DE68923883T2 (en) 1995-12-14
IL92122A0 (en) 1990-07-12
WO1990004643A1 (en) 1990-05-03
ATE161583T1 (en) 1998-01-15
IL92122A (en) 1996-06-18
JPH04501360A (en) 1992-03-12
DE68923883D1 (en) 1995-09-21
ATE126541T1 (en) 1995-09-15
EP0440723B1 (en) 1995-08-16
EP0440723A4 (en) 1992-05-20
JP2693248B2 (en) 1997-12-24
EP0440723A1 (en) 1991-08-14
US6521445B1 (en) 2003-02-18
EP0657544B1 (en) 1997-12-29
EP0657544A1 (en) 1995-06-14

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